A Thankful Moment

While there are certainly some aspects of being a CEO that are full of those proverbial thankless tasks…there are some moments that are just the opposite.  And boy are those rewarding.

I had one this morning.  While I frequently get nice emails or handwritten cards from employees after they interview or start or get a promotion or raise — and those are all great — this is one I can easily blog about because it’s online.

Yesterday was the first official day of work for Neil Schwartzman, who actually joined us many months ago as a consultant running compliance for our Sender Score Certified whitelist but just finally became a full-time employee as we set up a Canadian entity and International entity and whatever our lawyers and accountants told us we had to do in order to be legit about hiring out of the country.

Neil’s thank you post is very entertaining (I promise, our objective isn’t to have employees drinking and slacking off!), but more than that, rewarding in that he says we do a good job at Return Path of walking the walk around ethics, reputation, and high standards in what we do for the email ecosystem.  Now that’s rewarding.

But in some ways, it’s even more meaningful coming from Neil.  Just as he says he took a risk in coming to work with us, we took a risk in bringing him on board.  As a leading voice in the anti-spam community, Neil is exactly the kind of person that spooks out some of our clients who think of anti-spammers as the enemy.  Our view is, as you can imagine, more nuanced.  Anti-spammers who do their job well are a legitimate marketer’s best friend because they are keeping the inbox clean of actual spam.  As we tell our clients, we are a big tent here — the only way we will solve our clients’ deliverability problems is by working WITH the receivers of the world on common language, rules, standards, and metrics — not working AGAINST them.  And that’s where Neil has done such a great job for us so far — bringing his unique perspective on the spam problem and working alongside many others on our deliverability team like Tom Bartel, Tom Sather, Leslie Price, Melinda Plemel to help keep the world safe for email.

So thanks, Neil…and right back at you!

Try It On For Size

I’ve always been a big fan of taking a decision or a change in direction I’m contemplating and trying it on for size.  Just as you never know how a pair of pants is really going to fit until you slip them on in a dressing room, I think you need to see how decisions feel once you’re closing in on them.

Here’s why:  decisions have consequences.  No matter how prescient leaders are, no matter if they’ve been trained in chess-like (three-moves-ahead) thinking, they can almost never perfectly foresee all the downstream reactions and effects of decisions.  Figuring out how to create “mental fittings” is a skill that I think is critical for CEOs and other leaders.

When I try something on for size, I’m usually trying to accomplish one of a few things.  Sometimes, I’m simply trying to see how words sound when they come out of my mouth.  As Homer Simpson periodically muses, “did I think that, or did I say that out loud?”  There’s no substitute for articulating a new phrase, or theory, out in the open and seeing if it sounds the way YOU expect it to.  Other times, I’m trying to see how different messages or stories play with different audiences.  Will employees think it’s exciting when we announce X, or scary, or confusing?  Will a customer understand the new positioning of our company when you include the new product?  Will investors understand the story in 9 words or less?  Finally, there are times when my objective in trying something on for size is to understand specific downstream effects of a decision.  Throwing something out into the open and taking copious notes as people give you their “blink” concerns and reactions are invaluable.

Of course, the main thing to avoid when trying decisions or changes in direction on for size is creating chaos!  There are a few ways to create chaos.  One is by having your “try it on for size” conversation with an employee turn into a de facto decision because the employee takes your words and then deliberately acts on them.

Alternatively, the same thing could happen inadvertently because even though the employee knows intellectually not to act on your comments, he or she starts to incorporate them subconsciously, thinking they are likely to become the law of the land.

Another is by creating false expectations and disappointment if you decide an idea doesn’t fit when you try it on, and then you scrap it, leaving behind a trail of the idea for others to see and discuss.  All the same can be said with customers or investors or any other stakeholder.  Your words as CEO or any kind of a leader can be quite powerful, and trying something on for size can have real unintended consequences if not done carefully.

In all cases, the best antidotes are communication and judgment.  Make sure if you are trying something on for size internally that you communicate early and often to your audience that all you are doing is just that – trying something on, and follow up with people afterwards to make sure your intent really sunk in.  But judgment is also critical.  Pick your target audience for a fitting on carefully, make sure to blend trusted internal AND external associates, and make sure to rotate who you talk to about new things so you don’t develop a consistent bias in your idea generation.

I’d like to think that Mark Twain would wholeheartedly approve of me paraphrasing his famous quote for this purpose, but I’m getting a little tired of all these reports about how email is dead. The latest one comes in the form of an op-ed in Computerworld this week. This will be a longer post than usual — my apologies in advance.

The writer talks about how email will die soon because there are too many issues with viruses, spam, IT management costs, and employment practices. The writer says email is close to having a bigger downside than upside, and that email will go the way of the typewriter or the floppy disk drive.

I say that this is a writer who has a bad IT department or a bad email service, a stunning lack of faith in technology’s ability to overcome adversity, and perhaps a misunderstanding of basic economic productivity.

Email is alive and well, as far as I can tell:

– Consumer email adoption is huge and rising. Every time I see one of those market research surveys from Pew or NFO, email activity and adoption is on the rise. It’s the number one Internet-based activity, with nearly 100% of people using it and a huge percentage of those people addicted to it.

– Email business usage is now mission critical for most employees. Enough said, for this audience, anyway. Economic productivity gains from email usage are outpacing the costs of having email system administrators and spam filters by orders of magnitude. For a quick flashback, compare the time spent firing off an email to 5 members of your staff, cc’ing your boss, and bcc’ing two of your other colleagues to the analog analog of making phone calls, holding meetings, or dictating/longhanding a memo, typing it with carbon paper or even using a photocopier, then physically distributing it.

– Spam filters are getting better by the day. While there is still a cat-and-mouse game going on between spammers and spam filters that will always result in a certain amount of false positives (good email that gets filtered) or false negatives (spam that sneaks into your inbox anyway), how many heavy email users can honestly say that their actual inbox spam problem is worse now than it was a year ago? The false positive and false negative problems will be largely solved in one way or another within 24 months. They won’t be completely solved despite Bill Gates’ optimistic prognostications, but they’ll be well under control to the point of being inconsequential.

– People are signing up for email newsletters and marketing at astonishing rates. If email was on the way out, this is the single metric you’d expect to be falling as a precursor to the crash. Well, guess what? This metric is on the rise! My company alone is getting almost 80,000 people each day to sign up for our various email-related services. Many companies who sell direct to consumers online are generating upwards of 25% of their revenue via email. Those are not exactly the signs of a sick medium.

– The email industry will not allow itself go the way of the typewriter (by the way, you will note, there was never really a “typewriter industry” the way that email has turned into its own sector). There are simply too many companies, with too much at stake, with too much capital to invest and too much reward to be gained, to permit obsolesence.

For those of you who know that my company Return Path is in the email business, you may say that my comments are self-serving, and I suppose that’s true. I’m always open to a disruptive technology, but changing human behavior is much more difficult than replacing floppy disks with DVDs or hard drives, and at this point, email as a viable communication medium is much less about the technology than about human behavior. It takes a “super disruptive” technology to make that fundamental a change.

Perhaps the writer of that op-ed should think about another technology with much grizzlier characteristics that would be sure to put it on the verge of extinction. The technology is dirty. It’s smelly. It’s terrible for the environment. Some say it’s imperling the future of the planet. All it tries to do is a simple thing, but it can cost people who live at the U.S. median income level as much as 15% of their net income every year (all headier issues than those created by email). We all generally refer to that technology as the automobile. Does anyone think that the cars is going away soon?

As for the comparison of the typewriter to email, I’ll quote Twain again: “History doesn’t repeat itself – at best it sometimes rhymes.”

The Rumors of Email’s Demise Have Been Greatly Exaggerated, Part II

Fred beat me to it.  There was an interesting article floating around yesterday about how Korea, which is one of the cutting edge nations in terms of technology usage, is finding that younger people prefer electronic communications like SMS text messaging and IM to email.  Fred says he sees that trend here in his teenage kids as well.

It will be interesting to see how this develops.  It may be over the long haul that more personal communication happens over SMS and IM, but I’m still a believer in email for more formal business communications, any longer form note, and distribution of content or marketing that is best served on a larger screen and in a less intrusive way.

For Whom the Bell Tolls

I don’t understand why everyone in the world hasn’t yet signed up for VOIP services from companies like Vonage. We just did it a couple of weeks ago at home. In terms of quality, it’s virually indistinguidhable from a POTS land line. You can have as many numbers as you want on the same account. TiVo works with it. You can keep your old phone number. There are no minimums and no contracts. They don’t have to come to your house to get it to work. They’ve even figured out how to get 911 and 311 to work with it.

It’s got tons of other cool features, as well, but even if all you do with it is use it like your old phone or fax line, all it costs is $15/month with a $40 startup cost for 500 minutes/month (they also have $25/month for unlimited calling). I hate to sound like an ad for the thing, but it’s just a better way of having a phone at home. The only real risk is an outage with your cable modem, and while that does happen from time to time, most people now have cell phones as a backup, and if your modem is out, calls go straight into voicemail.

We’ve had one or two phone lines at home forever and bounced around over the years from Verizon to Sprint to AT&T depending on who had the best deal of the month. No matter which carrier we’ve used, we don’t use our home phone that much, and we’ve always paid between $50-100/month per line for the privilige. No longer!

Anyway, I don’t know much about Vonage, and they may have tons of competitors. From a business perspective, then, I don’t know who is going to win this war…but as my board member Greg Sands says, I certainly know who’s going to lose it. I wouldn’t want to be a big old phone company today!

Why is Seth Godin so Grumpy?

Permission marketing guru Seth Godin says we should all Beware the CEO blog. His logic? Blogs should have six characteristics: Candor, Urgency, Timeliness, Pithiness, Controversy, and maybe Utility — and apparently in his book, CEOs don’t possess those characteristics.

Certainly, CEOs who view blogs as a promotional tool are wasting their time, or are at least missing a fundamental understanding about the power of blogs and interactivity.

But many of the ones I read (and the one I write) do their best to be anything but promotional. One of my colleagues here describes my blog as “a peek inside the CEO’s head,” which is a great way of putting it. And I still stand by my earlier posting about the value of the blog to me and to the company — hardly “annual report fluff.”

How’s that for honest, timely, controversial, and pithy, Seth?

When Do You Hire a Real Head of Sales?

A fellow entrepreneur I’m friendly with who’s got a really early stage company asked me the other day when he should hire his first head of sales.

I think the answer completely depends on what kind of business you’re in and how dependent it is on external relationship building, and also what kind of entrepreneur you are. But I tried to distill my answer down to three things for him to think about:

If your company requires a meaningful amount of customer participation before your initial product is launched, you need to invest in sales months ahead of anticipated revenue. This was the case for us at Return Path. We hired our first head of sales five months before our anticipated launch because we needed to have 10-12 beta customers on board in order to have a successful launch.

If you can wait until your product is developed and ready to ship before selling it, you can afford to wait longer if you’re handling early market development and requirements yourself. However, when you find that you don’t have time to call back interested high value prospects within a single business day because of competing priorities to get your business off the ground, it’s definitely time to bring someone in. This is especially true if you’re in a buzz business where you have prospects calling YOU to ask if they can try out your product or service.

Finally, in either case, the trick is timing. The moment you actually need a head of sales is too late to start looking for one, since that process can take a few months. So what you have to do is make your best effort at figuring out 2-3 months ahead of time when that urgent need will pop up and start your recruiting efforts then.

More thoughts on some of Fred’s and Brad’s points about VC deal algebra, valuation, and liquidation preferences for venture-funded startups. My apologies if this gets a little too technical or too long!

On liquidation preference: Preferred stock makes sense, participating preferred makes less sense. Sure, a VC who puts capital at risk in a startup should be entitled to get his or her money out before management and common shareholders who are paid to run the business. But I’ve always had an issue (even when I was in the venture business, although admittedly not as a partner) with the participating preferred security which allows VCs to get their money out first, and then still receive their proportional share of the rest. Fred calls this “a loan with an option,” and that’s the best presentation I’ve ever heard of the security. But what’s always struck me as a bit over the top about this is that it gives VCs downside protection at the same time they’re negotiating even more upside in a deal.

One simple solution to this, if you can negotiate it, is a “kickout” provision which makes the participation feature on the security go away if the company becomes worth a multiple (usually 2x or 3x) of the post-money valuation of the financing. In other words, it gives the VC the downside protection they want but gives you and other shareholders more of the upside if things go really, really well.

On valuation and deal algebra: I completely agree that valuation is a derived number and that it’s completely misunderstood in early stage investing. However, I think that while there may be low correlation between valuation and what the business is worth today, there are a few things that have always bugged me about VC valuations:

While I understand that valuation is more a function of future potential than current value, it sometimes feels like companies get punished for having a track record. Let me clear about my point – it’s not that that I actually think VCs lower valuations unfairly when companies demonstrate poor results. It’s actually the opposite. VCs are quick to bid up the valuation on companies that don’t have revenue or even a lot of operations just because the idea is cool or because the theoretical market is large (Friendster, anyone?). I don’t think VCs as a group do a good enough job of risk-adjusting or future-competition-adjusting valuations for new companies, or they get caught up in what Fred once called Venture Fratricide and just pour money into new sectors en masse. This has the unintended side effect of making management teams of existing companies feel like their ideas aren’t interesting any more because they’re not new and shiny.

Second, it’s interesting to note that while VCs use valuation as a way of placing limits and getting protection on their bet about the future potential of the company and entrepreneur, entrepreneurs have no corresponding mechanism to place limits or receive protection against having a bad VC. (VCs actually have many tools at their disposal to reign in poorly performing management teams once the deal is signed – they can fire them, cram them down, force all their common stock to be on a vesting schedule or subject to clawback.) But make no mistake about it – a bad VC can almost kill a company, or certainly keep it from realizing its full potential, and once that deal is signed, the entrepreneur typically has little recourse. I’m not sure there’s an easy solution to this particular problem either, but it’s one that’s worth thinking through with a good lawyer the next time you negotiate a term sheet with a new venture investor (and certainly one that is easier to negotiate if you either have a good track record as an entrepreneur or multiple VCs interested in your company). I made one suggestion around participation in future financings in my earlier posting on term sheet negotiations — item #8.

The final thing that’s bugged me about valuations stems from what Fred calls the 1/3 rule (1/3 of a VC’s investments work out well, 1/3 go sideways, 1/3 go bad). As a result of the rule, valuations and deal structures can end up being about VCs getting as much upside as possible out of their winning deals to cover their losses from their zero-return deals. What bugs me about this is that entrepreneurs don’t have that same luxury of a diversified portfolio – they are 100% invested in terms of their human capital and often their investment capital in their company. I fully realize that this is the nature of the beast, but I’ve always felt as a result that entrepreneurs should negotiate – and VCs should be willing to give – proportionally much more upside to management in the event that the deal turns out to be a big winner. This point relates back to my first point about participating preferred securities.

Next up in this series…Reverse Engineering Venture Economics, and managing other kinds of investors (Angel and Strategic).

This is another in a series of postings that relate to Fred’s and Brad’s various postings about venture capital funding. (Please note I have added an 11th item in response to a comment by Jack Sinclair, Return Path’s VP of Finance and my partner in crime on all transactions for the past five years.)

I think the most important part of the venture financing process is negotiating the term sheet. Although they’re only 2-3 pages long, term sheets contain summaries of all the critical aspects of a financing, and once they’re signed, the remainder of the financing process is significantly more “automatic.” Based on the financings I’ve seen and worked on – both as a VC and as an entrepreneur – my Top 10 (now 11) biggest takeaways for entrepreneurs are as follows (not in any particular order):

1. Get a good lawyer. I mean a really good one. Not just one who you are comfortable with and who is productive and doesn’t charge you too much (as Brad says, your wife’s brother’s friend’s neighbor), but one who knows venture financings like the back of his or her hand. They’re out there, many of them have worked on both sides of these transactions – for VCs and for entrepreneurs, and they can save your ass. No matter how many deals you’ve worked on, your lawyer has worked on more of them. Return Path’s lawyer, David Albin from Finn Dixon & Herling, is great if you need one.

2. Focus on terms that matter, otherwise known as Pick your battles. A typical VC term sheet will have at least 20 terms spelled out in it. There are only a few that really matter in the end, although you should at least make sure your lawyer is comfortable that the others are reasonable and somewhat standard. Spend time on valuation, the type of security, the option pool, Board composition, and your own compensation and rights.

2a (new). Sacrifice valuation for a clean security. Everyone always thinks that price/valuation is the most important thing to maximize in a deal. However, the structure of the security can be much more important in the long run. Whether the VCs buy 33% of your company or 30% of your company is much less important than having a capital structure that’s easy for an outsider to understand and want to join (e.g., investment banker or later-stage VC).

3. Always have a BATNA (Best Alternative to a Negotiated Agreement – a fancy way of saying Plan B). This is probably the most important piece of advice I can offer, and it extends to any negotiation, not just term sheets. If you have two or three VCs who are interested in funding you, I can guarantee you will end up with better terms from the highest quality investor in the group if you play the negotiation well. If you have one term sheet, you have zero leverage in your negotiation. Yes, you will spend 2-3x the amount of time on the process, but it’s well worth it.

4. Be prepared to pay up for high quality investors. There is a world of difference between good VCs and bad VCs (both the individual partners and the firms) that will ultimately have a lot to do with how successful your company can become. The quality of your VC isn’t more important than the quality of your product or your team, but it’s right up there. But – and this is an important but – you should expect to “pay” for quality in the form of slightly weaker terms (whether valuation or type of security). This is where having a BATNA really comes in handy.

5. Ask for references. Don’t be shy – prospective VCs are checking up on you…you have every right to do the same with them. Ask them for references of CEOs they’ve worked with. Ask them for a CEO they’ve had to fire as a reference. The good ones will give you the full roster of everyone they’ve ever funded and tell you to call anyone. The bad ones will give you two names and ask for time to prep them ahead of time.

6. Don’t let the VC get away with negotiating a point by saying “we always do it this way.” That’s just not true. VCs may have a preferred way of doing deals or handling a specific term, but every deal they’ve ever done is different, and they know it. If there’s a compelling reason for them to insist on a particular term, you have the right to hear it (if it’s important to you).

7. If you have multiple investors in the syndicate, insist on a single investor counsel and a lead investor. This is essential to (a) protect your sanity, and (b) prevent you from paying zillions of dollars in legal fees. You have to make the VCs stick to it, though – they can’t come back and re-trade the deal after it’s been negotiated. This is also helpful in getting a syndicate cooperating with each other and aligning the members’ interests, particularly if it has investors who have participated in different rounds of the company’s financing. Do expect to play moderator constantly throughout the process, however, to ensure that it goes smoothly.

8. Try do deal in advance with follow-on financings. When an investor doesn’t participate in a follow-on financing, it creates a total nightmare for you. Other investors will want to punish their wayward colleague and can create massive collateral damage in the process to common shareholders and management. Just as VCs will insist on something called “pre-emptive rights” (the right to invest in future financings if they want), you and your lawyer should insist on some protection in the event that one of your investors abandons you when you are raising more capital.

9. Handle the term sheet negotiation carefully. Whether it’s an initial round or a follow-on round, how you handle yourself in this negotiation sets the tone for the next stage of your relationship with the VC. The financing is the line of demarcation between you and the VC courting each other, and the VC joining your board and effectively becoming your boss.

10. Finally don’t forget to say thank you at the end of the process. Whether you send a formal email, a handwritten note, or a token gift, be sure to thank your VCs after a financing. They’re putting their butt on the line for your company, they’re investing in YOU, and they’re making it possible for you to pursue your dream. That deserves a thoughtful thanks in my book.

Sorry for the long posting. The next one or ones in this series will be on valuation, preferences, and “Venture Capital deal algebra.”

There was a great essay in the New York Times yesterday about multitasking. The gist of the article is that multitasking, when taken to an extreme, is unproductive at best and in the case of driving, quite dangerous.

I’ve long believed that in business, as in any activity relying in part on interpersonal relationships, it’s important to be fully present when talking to other people. This is especially true in one-on-one conversations, but true even in larger meetings. The article talks about the clicking you hear when you’re talking to someone on the phone and he or she is typing in the background. And we’ve all been in meetings where someone picks up a Blackberry to reply to a presumably non-urgent email. How annoying! Better to step out of the meeting if the email is that important…or tell the person who called you that you don’t have time to talk now.

Even forgetting the annoying part, how can you possibly connect with another person when you’re reading or writing at the same time? How can you make a point or read their body language? How can you convey to the rest of the room that you’re taking the subject seriously?

Like most of us these days, I too am addicted to multitasking, repsonding to emails, answering cell phones, and the like. The only way I’ve been able to make sure I focus on the meeting at hand is to turn off the phone, leave the Blackberry or laptop in another room, bring nothing other than a piece of paper and pen to the meeting. Sure, I have to go back and enter a couple things on my computer in my to-do list afterwards instead of in real time, but it’s a worthwhile tradeoff. If I’m on the phone, I turn away from my desk or put my headset on and walk around the office to remove other temptations.

I don’t think all multitasking is bad…in fact there are lots of times where it makes great sense and is productive. But the principle of Anything Worth Doing is Worth Doing Well applies here in spades — having a conversation with another person, or being fully present and accounted for in a meeting, are usually worth doing well!

Go Ahead…Make My Day

I’ve taken to smiling and giving a simple wave to fellow joggers out in Hudson River Park on Manhattan’s lower west side, especially at off times like early mornings and late nights.  Call it the fellowship of the urban exerciser, blame it on the endorphines, whatever.  I’ve also noticed that very few people respond, even when they clearly notice.  So I tried a little experiment this morning and kept a running count (yes, pun intended).

Of the roughly 30 people I passed this morning, I’d say 15 made no acknowledgment whatsoever of my friendliness, although they clearly noticed it.  Another 7 gave me a weird look like I was nuts (perhaps not wholly incorrect).  5 were "in the zone" and legitimately didn’t notice.  A mere 2 smiled or waved back.  But the best was the very last person I passed towards the end of my run, who I ended up standing next to for a minute while I was stretching/cooling down.

Her comment:  "It’s so nice to know that there are some people who are friendly to strangers here in New York.  Thanks for making my day."  Go ahead — be 10% more friendly or smiley today.  See what effect it has on people around you.  Make someone’s day!